Diethyl Ether → Tert-butyl 6-azaspiro[2.5]octane-6-carboxylate

To a mixture of diethyl ether (25 mL) and 30% aqueous potassium hydroxide solution (5 mL) was added 1-methyl-3-nitro-1-nitrosoguanidine (containing 50% water, 2.17 g), and the mixture was stirred at room temperature for 10 min. To a solution (25 mL) of tert-butyl 4-methylidenepiperidine-1-carboxylate (1.00 g, 5.07 mmol) in tetrahydrofuran was added dropwise the above-mentioned ether layer, and the mixture was stirred at room temperature for 16 hr. To the reaction mixture was added a ether layer prepared from diethyl ether (25 mL), 30% aqueous potassium hydroxide solution (5 mL), and 1-methyl-3-nitro-1-nitrosoguanidine (containing 50% water, 3.77 g), and the mixture was further stirred for 16 hr. To the reaction mixture was added acetic acid (1 mL), and the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→90/10) to give the title compound (261 mg, 24%) as a white powder.

1. stirringthe mixture was stirred at room temperature for 16 hr
2. stirringthe mixture was further stirred for 16 hr
3. concentrationthe mixture was concentrated under reduced pressure
4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→90/10)

ORDレコード

ord-a2409fcde66f48d09a9018bafa926910

出典データセット

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08344135B2